Oenanthotoxin
Names | |
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Preferred IUPAC name
(2E,8E,10E,14R)-Heptadeca-2,8,10-triene-4,6-diyne-1,14-diol | |
Other names
Enanthotoxin
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C17H22O2 | |
Molar mass | 258.361 g·mol−1 |
Melting point | 86 °C (187 °F; 359 K) |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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0.58 mg/kg for mice |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oenanthotoxin is a
Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin.Occurrence
Oenanthotoxin concentration in plants is dependent on seasonal changes and geographical location, the most is present during late winter and early spring.[8] Contrary to most poisonous plants that contain bitter tastes or burning sensations, the water dropwort has a rather sweet and pleasant taste and odor.[9] Water dropwort is characterized by a yellow liquid that changes color due to air exposure.[1][9] The roots are the most toxic part, although the entire plant contains poisonous properties.[8][10]
History and culture
The discovery and use of plants containing oenanthotoxin predates Socrates and Homer and its first use as a poison is thought to have been implemented between 1800 BC and 800 BC in Pre-Roman Sardinia.[9][11] In Ancient Sardinia, it was considered to be a humane form of euthanasia. Elderly people who were unable to care for themselves were given water dropwort and dropped from a high rock to ensure death.[9][11] It is also believed that Socrates ingested the plant when executed.[12]
A common symptom of oenanthotoxin is risus sardonicus, better known as the Sardonic Grin, coined by Homer in the 8th century BC, due to the victim's rigid smile after ingestion.
Furthermore, as a muscle relaxant, it is believed to have cosmetic
Mechanism of action
Although oenanthotoxin is a relatively well known poison, its mechanism of action is not entirely understood. However, there is evidence that its mechanism of action is similar to that of cicutoxin.
Oenanthotoxin is part of a group of C17 conjugated
Symptoms
Oenanthotoxin is extremely dangerous and toxic (LD50 = 0.58 mg/kg for mice),[1] there have been numerous case studies documenting the common symptoms including: convulsions, seizures, nausea, diarrhea, tachycardia, mydriasis, rhabdomyolysis, renal failure, respiratory impairment, and cardiac dysrhythmias.[1][8][9]
Below is a comprehensive table listing the recorded symptoms caused by oenanthotoxin within each system in the body Oenanthe crocata:[1]
Organ system | Symptoms |
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Neurological | slurred speech, dizziness, paresthesia, delirium, ataxia, coma, seizures, trismus, hyperreflexia, opisthotonus, spasms, cerebral edema, status epilepticus |
Gastrointestinal | nausea, vomiting, salivation, abdominal pain |
Respiratory | congestion, distress, depression, airway obstruction, arrest, apnea |
Cardiovascular | tachycardia, brachycardia , hypertension, hypotension, cardiac dysrhythmias, cardiac arrest
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Renal | glycosuria, proteinuria, hematuria, oliguria, myoglobinuria, acute renal failure |
Musculoskeletal | weakness, muscle spasms, muscle rigidity, rhabdomyolysis |
Metabolic | elevated temperature, liver dysfunction, hypokalemia, lactic dehydrogenase, disseminating (intravascular, coagulation), metabolic acidosis, azotemia |
Occular | mydriasis |
Dermal | diaphoresis, cyanosis , flushed face
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References
- ^ S2CID 21855822.
- PMID 19245244.
- .
- ^ E. G. C. Clarke, D. E. Kidder and W. D. Robertson (1949) J. Pharm. Pharmacol. 1 377-381
- .
- S2CID 19201342.
- ^ Anet, E. F. L. J.; Lythgoe, B.; Silk, M. H. & Trippett, S. (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry and Industry. 31: 757–758.
- ^ a b c "Information Sheet: 31 Hemlock Water Dropwort (Oenanthe crocata)" (PDF). Centre for Ecology & Hydrology. Centre for Aquatic Plant Management. Archived from the original (PDF) on 2015-02-24. Retrieved 2019-05-01.
- ^ PMID 19245244
- .
- ^ a b c Owen, James. "Ancient Death-Smile Potion Decoded?". National Geographic. Journal of Natural Products. Archived from the original on June 5, 2009. Retrieved June 2, 2009.
- ^ Bletchly, Rachael. "Killers in your garden; Beware these poison plants". The Free Library. Gale, Cengage Learning.